Ammonium Chloride → HCID 59716617, Verbindung

HRID 2224231Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2224231
[CH3:1][Mg+].[Br-].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[N:15][N:14]3[C:17](=[O:27])[N:18]([CH2:20][C:21](=[O:26])[CH2:22][O:23][CH2:24][CH3:25])[N:19]=[C:13]3[C:12]=2[C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:7][CH:6]=1.[NH4+].[Cl-]>>[Cl:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[N:15][N:14]3[C:17](=[O:27])[N:18]([CH2:20][C:21]([OH:26])([CH3:1])[CH2:22][O:23][CH2:24][CH3:25])[N:19]=[C:13]3[C:12]=2[C:28]2[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[CH:9][CH:10]=1

Komponenten

4

Edukt 3

HCID 25517Ammonium ChlorideHCID 597168797,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-oneHCID 178418689HCID 178418689, Verbindung

Produkt 1

HCID 59716617HCID 59716617, VerbindungAusbeute 16 %

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

MeMgBr (0.03 mL, 0.08 mmol, 3.0 M in Et2O) was added to a solution of 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-oxopropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one, prepared as described in Example 30, (23 mg, 0.05 mmol) at −78° C. The reaction was stirred for 30 min. at −78° C. After this time, saturated aqueous NH4Cl (2 mL) was added to the reaction and the resultant solution was warmed to RT. The layers were separated and the aqueous layer was extracted with EtOAC (3×10 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated. The crude product was purified by reverse phase HPLC to give the title compound, 7,8-bis(4-chlorophenyl)-2-(3-ethoxy-2-hydroxy-2-methylpropyl)-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one (4 mg, 16% yield) as a yellow oil. MS [M+H]+: found 473; 1H NMR (CDCl3, 400 MHz) δ 8.13 (s, 1H), 7.29-7.18 (m, 6H), 7.06-7.02 (m, 2H), 4.25 (d, 1H), 3.98 (d, 1H), 3.43 (q, 2H), 3.35 (d, 1H), 3.25 (d, 1H), 1.18 (s, 3H), 1.07 (t, 3H).

Aufarbeitung

  1. customprepared
  2. customas described in Example 30, (23 mg, 0.05 mmol) at −78° C
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with EtOAC (3×10 mL)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5d6a36b0aee0460cb43fb34f44256eac
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07378418B2

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